JP6357223B2 - 多段凝縮を用いるアルデヒド製造方法 - Google Patents
多段凝縮を用いるアルデヒド製造方法 Download PDFInfo
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- JP6357223B2 JP6357223B2 JP2016511723A JP2016511723A JP6357223B2 JP 6357223 B2 JP6357223 B2 JP 6357223B2 JP 2016511723 A JP2016511723 A JP 2016511723A JP 2016511723 A JP2016511723 A JP 2016511723A JP 6357223 B2 JP6357223 B2 JP 6357223B2
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- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 238000009833 condensation Methods 0.000 title description 16
- 230000005494 condensation Effects 0.000 title description 16
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title 1
- 239000007788 liquid Substances 0.000 claims description 168
- 150000001336 alkenes Chemical class 0.000 claims description 68
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 46
- 238000007037 hydroformylation reaction Methods 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 38
- 239000000047 product Substances 0.000 claims description 33
- 150000001299 aldehydes Chemical class 0.000 claims description 31
- 230000008569 process Effects 0.000 claims description 22
- 230000015572 biosynthetic process Effects 0.000 claims description 19
- 238000003786 synthesis reaction Methods 0.000 claims description 19
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical group CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 5
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical group CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 239000012263 liquid product Substances 0.000 claims 19
- 239000007789 gas Substances 0.000 description 87
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LGAQJENWWYGFSN-PLNGDYQASA-N (z)-4-methylpent-2-ene Chemical compound C\C=C/C(C)C LGAQJENWWYGFSN-PLNGDYQASA-N 0.000 description 1
- FSHNFAOXXJLGJE-UHFFFAOYSA-N [Rh].[P] Chemical compound [Rh].[P] FSHNFAOXXJLGJE-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical class CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- -1 ethylene, propylene Chemical group 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/783—Separation; Purification; Stabilisation; Use of additives by gas-liquid treatment, e.g. by gas-liquid absorption
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/002—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by condensation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
- C07C45/505—Asymmetric hydroformylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201361817506P | 2013-04-30 | 2013-04-30 | |
US61/817,506 | 2013-04-30 | ||
PCT/US2013/069382 WO2014178912A1 (en) | 2013-04-30 | 2013-11-11 | Aldehyde production process with multi-stage condensation |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2016520579A JP2016520579A (ja) | 2016-07-14 |
JP2016520579A5 JP2016520579A5 (fi) | 2016-12-28 |
JP6357223B2 true JP6357223B2 (ja) | 2018-07-11 |
Family
ID=49622918
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016511723A Active JP6357223B2 (ja) | 2013-04-30 | 2013-11-11 | 多段凝縮を用いるアルデヒド製造方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US9340480B2 (fi) |
EP (1) | EP2991957B2 (fi) |
JP (1) | JP6357223B2 (fi) |
CN (1) | CN105164094B (fi) |
PL (1) | PL2991957T5 (fi) |
TW (1) | TWI494299B (fi) |
WO (1) | WO2014178912A1 (fi) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6357223B2 (ja) | 2013-04-30 | 2018-07-11 | オクシア・コーポレーション | 多段凝縮を用いるアルデヒド製造方法 |
JP6889179B2 (ja) * | 2016-03-18 | 2021-06-18 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | ヒドロホルミル化プロセス |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3379768A (en) * | 1965-06-01 | 1968-04-23 | Koppers Co Inc | Method of producing hydratropic aldehyde |
US4148830A (en) | 1975-03-07 | 1979-04-10 | Union Carbide Corporation | Hydroformylation of olefins |
EP0016285B2 (en) | 1979-03-21 | 1986-03-05 | DAVY McKEE (LONDON) LIMITED | Process for the production of valeraldehydes by hydroformylation of butene-1 |
DE3114147A1 (de) | 1981-04-08 | 1982-10-28 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gewinnung von aldehyden |
DE3412336C2 (de) | 1984-04-03 | 1994-03-31 | Hoechst Ag | Verfahren zur Hydroformylierung von Propylen |
US4593127A (en) | 1985-01-11 | 1986-06-03 | Union Carbide Corporation | Hydroformylation process |
US4640743A (en) | 1985-04-24 | 1987-02-03 | Shell Oil Company | Multi-stage condensation process |
US4827043A (en) * | 1988-01-22 | 1989-05-02 | Eastman Kodak Company | Impurity removal from carbon monoxide and/or hydrogen-containing streams |
JP2893902B2 (ja) | 1989-10-19 | 1999-05-24 | 三菱化学株式会社 | オレフィンのヒドロホルミル化法 |
US5087763A (en) | 1990-11-09 | 1992-02-11 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process |
US5367106A (en) | 1993-09-20 | 1994-11-22 | Hoechst Celanese Corporation | Coupled secondary oxo reaction system |
US5361589A (en) * | 1994-02-04 | 1994-11-08 | Air Products And Chemicals, Inc. | Precooling for ethylene recovery in dual demethanizer fractionation systems |
JPH0899930A (ja) * | 1994-10-03 | 1996-04-16 | Mitsubishi Chem Corp | テレフタル酸の製造方法 |
JP4080555B2 (ja) * | 1994-12-09 | 2008-04-23 | 三菱化学株式会社 | アルデヒド類の製造方法 |
US5648553A (en) | 1994-12-09 | 1997-07-15 | Mitsubishi Chemical Corporation | Method for producing aldehydes |
FR2735989B1 (fr) | 1995-06-29 | 1997-08-14 | Rhone Poulenc Nutrition Animal | Procede et installation de purification d'un flux gazeux contenant de l'acroleine |
JP2001342164A (ja) * | 2000-03-30 | 2001-12-11 | Mitsubishi Chemicals Corp | アルデヒド類の製造方法 |
JP2001342162A (ja) * | 2000-03-30 | 2001-12-11 | Mitsubishi Chemicals Corp | アルデヒド類の製造法 |
JP3864668B2 (ja) * | 2000-05-01 | 2007-01-10 | 三菱化学株式会社 | アルデヒド類の製造方法 |
DE10034360A1 (de) * | 2000-07-14 | 2002-01-24 | Oxeno Olefinchemie Gmbh | Mehrstufiges Verfahren zur Herstellung von Oxo-Aldehyden und/oder Alkoholen |
DE102007061648A1 (de) * | 2007-12-20 | 2009-07-02 | Evonik Oxeno Gmbh | Mehrstufiges kontinuierliches Verfahren zur Hydroformylierung von höheren Olefinen oder Olefingemischen |
DE102008002187A1 (de) * | 2008-06-03 | 2009-12-10 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von C5-Aldehydgemischen mit hohem n-Pentanalanteil |
CN202148269U (zh) * | 2011-07-08 | 2012-02-22 | 南京荣欣化工有限公司 | 一种氢甲酰化反应中有机相的分离装置 |
JP6357223B2 (ja) | 2013-04-30 | 2018-07-11 | オクシア・コーポレーション | 多段凝縮を用いるアルデヒド製造方法 |
-
2013
- 2013-11-11 JP JP2016511723A patent/JP6357223B2/ja active Active
- 2013-11-11 EP EP13793050.9A patent/EP2991957B2/en active Active
- 2013-11-11 US US14/782,694 patent/US9340480B2/en active Active
- 2013-11-11 WO PCT/US2013/069382 patent/WO2014178912A1/en active Application Filing
- 2013-11-11 PL PL13793050T patent/PL2991957T5/pl unknown
- 2013-11-11 CN CN201380076052.0A patent/CN105164094B/zh active Active
-
2014
- 2014-02-10 TW TW103104236A patent/TWI494299B/zh active
Also Published As
Publication number | Publication date |
---|---|
PL2991957T5 (pl) | 2020-08-10 |
CN105164094A (zh) | 2015-12-16 |
CN105164094B (zh) | 2016-10-12 |
US9340480B2 (en) | 2016-05-17 |
US20160068460A1 (en) | 2016-03-10 |
EP2991957A1 (en) | 2016-03-09 |
JP2016520579A (ja) | 2016-07-14 |
EP2991957B2 (en) | 2020-02-19 |
TWI494299B (zh) | 2015-08-01 |
EP2991957B1 (en) | 2017-04-26 |
WO2014178912A1 (en) | 2014-11-06 |
TW201441184A (zh) | 2014-11-01 |
PL2991957T3 (pl) | 2017-08-31 |
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